Phenylboronic Acid → HCID 11288679, compound

HRID 2106393Notes

Reaction equation

C(OC([N:8]1[CH:17]([CH3:18])[CH2:16][C:15]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]([CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N1C(C2C=CC=CC=2)=C2C(CCNC(C)C2)=N1)(C)C>>[CH:19]([N:13]1[C:12]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:11]2[C:15]([CH2:16][CH:17]([CH3:18])[NH:8][CH2:9][CH2:10]2)=[N:14]1)([CH3:20])[CH3:21]

Participants

Reactant 3

HCID 66827Phenylboronic Acid

HCID 59752605HCID 59752605, compound

HCID 86598398HCID 86598398, compound

Product 1

HCID 11288679HCID 11288679, compoundYield 64.3%

Procedure

The title compound (102 mg) was prepared as in Example 263 using 260 mg of 2-isopropyl-7-methyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (as outlined in Example 308 replacing cyclopentyl hydrazine with isopropyl hydrazine) and 101 mg of phenylboronic acid. The reaction sequence also yielded 2-isopropyl-5-methyl-3-phenyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene. MS (ESI): exact mass calculated for C17H23N3, 269.19; found, m/z 270.5 [M+H]+. 1H NMR (600 MHz, CD3OD): 7.58-7.52 (m, 3H), 7.36-7.35 (m, 2H), 4.43 (m, 1H), 3.65-3.57 (m, 1H), 3.51-3.48 (m, 1H), 3.23-3.11 (m, 3H), 2.87-2.82 (m, 2H), 2.76-2.73 (m, 1H), 1.48 (d, J=6.4 Hz, 3H), 1.43-1.40 (m, 6H).

Sources & evidence

ORD record: ord-a5451266144a43f592317a6fa3e19354
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579470B2

Reaction notes

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